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Intramolecular Cyclization of Alkenyl Alcohols: Towards the Synthesis of Oxacycles

Department of Organic Chemistry, Faculty of Science, Campus Miguel Delibes, 47011 Valladolid, Spain
Department of Material Science and Engineering, Industrial Engineering Faculty, Paseo del Cauce 59, 47011 Valladolid, Spain
Author to whom correspondence should be addressed.
Presented at the 24th International Electronic Conference on Synthetic Organic Chemistry, 15 November–15 December 2020; Available online:, accessed on 16 No-vember 2020.
Published: 16 November 2020
The presence of tetrahydropyrans and other sized oxacycles in natural products with interesting pharmacological properties has prompted researchers to try to develop new strategies for their selective synthesis. Moreover, these methodologies enable the introduction of structural modifications in the molecule for the synthesis of analogues with potential biological activity. An attractive atom economy process for the synthesis of these scaffolds is the intramolecular hydroalkoxylation of alkenes. However, this method has several drawbacks (such as the lack of generality and the presence of multiple side reactions) which have diminished its development. For many years, our research group has been devoted to developing different strategies for the regio- and stereoselective synthesis of oxygen and nitrogen heterocycles. Herein, we present our results on the effective acid catalyzed cyclization of alkenyl alcohols which bear a silyl group in their structure. As we will show, the presence of the silicon group is necessary for the cyclization to take place. Moreover, the cyclization towards tetrahydropyrans occurs with high stereoselectivity.
Keywords: Heterocycles; cyclizations; organosilanes; tetrahydropyrans Heterocycles; cyclizations; organosilanes; tetrahydropyrans
MDPI and ACS Style

González-Andrés, P.; Díez-Poza, C.; Fernández-Peña, L.; Cherubin, A.; Blanco, Y.; Barbero, A. Intramolecular Cyclization of Alkenyl Alcohols: Towards the Synthesis of Oxacycles. Chem. Proc. 2021, 3, 117.

AMA Style

González-Andrés P, Díez-Poza C, Fernández-Peña L, Cherubin A, Blanco Y, Barbero A. Intramolecular Cyclization of Alkenyl Alcohols: Towards the Synthesis of Oxacycles. Chemistry Proceedings. 2021; 3(1):117.

Chicago/Turabian Style

González-Andrés, Paula, Carlos Díez-Poza, Laura Fernández-Peña, Alberto Cherubin, Yolanda Blanco, and Asunción Barbero. 2021. "Intramolecular Cyclization of Alkenyl Alcohols: Towards the Synthesis of Oxacycles" Chemistry Proceedings 3, no. 1: 117.

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